Benzothiophene

Base Information

• Chemical Name: Benzothiophene
• CAS No.: 11095-43-5
• Deprecated CAS: 11095-43-5
• Molecular Formula: C8H6S
• Molecular Weight: 134.1982
• European Community (EC) Number: 202-395-7
• NSC Number: 47196
• UNII: 073790YQ2G
• DSSTox Substance ID: DTXSID2052736
• Nikkaji Number: J3.019.265F,J4.710D
• Wikipedia: Benzothiophene
• Wikidata: Q419709
• Metabolomics Workbench ID: 55217
• ChEMBL ID: CHEMBL87112
• Mol file: 11095-43-5.mol

Synonyms:benzo(b)thiophene;benzothiophene;thianaphthene

Chemical Property of Benzothiophene

Chemical Property:

• Vapor Pressure: 0.163mmHg at 25°C
• Melting Point: 28-32℃
• Refractive Index: 1.675
• Boiling Point: 221 °C at 760 mmHg
• Flash Point: 62 °C
• PSA: 0.00000
• Density: 1.187 g/cm³
• LogP: 0.00000
• Water Solubility.: insoluble
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 134.01902136
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

98%,99%, ^*data from raw suppliers

Benzothiophene 97 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R22:
• Hazard Codes: Xn:Harmful
• Statements: R22:

MSDS Files:

Useful:

• Chemical Classes: Other Classes -> Thiophenes
• Canonical SMILES: C1=CC=C2C(=C1)C=CS2

Technology Process of Benzothiophene

There total 216 articles about Benzothiophene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

phenylmercaptoacetaldehyde dimethyl acetal (99172-76-6) → diphenyldisulfane (882-33-7) + Benzo[b]thiophene (95-15-8,11095-43-5)

Guidance literature:

K₁₀-ZnCl₂; In gas; at 300 ℃;

DOI:10.1021/jo00112a010

Reference yield: 68.0%

bis (2-chloroethyl) sulphide (505-60-2) + acetylene (74-86-2,25067-58-7) → thiophene (188290-36-0,8014-23-1,25233-34-5) + carbon disulfide (75-15-0,12122-00-8) + Benzo[b]thiophene (95-15-8,11095-43-5) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With disulfide oil; at 650 ℃; for 1.75h; Further byproducts given;

DOI:10.1007/s11178-005-0260-5

Reference yield: 50.0%

benzothiaferrole (12086-84-9) → iron pentacarbonyl (13463-40-6,37220-42-1) + Benzo[b]thiophene (95-15-8,11095-43-5)

Guidance literature:

With CO; In hexane; loading an autoclave cup with Fe-compound in hexane and CO (500 psig, 25°C), heating (160°C, 700 psig, 19 h); cooling, transferring of soln. to a Schlenk flask (N2), GC and IR;

DOI:10.1021/om00095a024

upstream raw materials:

piperidine

3-Bromothianaphthene

styrene

3-hydroxybenzothiophene

Downstream raw materials:

3-(2-methylbenzoyl)benzothiophene

1-benzo[b]thiophen-3-yl-propan-1-one

benzo[b]thiophen-3-yl(phenyl)methanone

3-(4-methoxybenzoyl)benzothiophene

Refernces

• 1、 Moore,Greensfelder. "-". . p. 2008. Retrieved 1947.
• 2、 Litvinov,Ostapenko. "-". . . Retrieved 1971.
• 3、 Hansch,Hawthorne. "-". . p. 2495. Retrieved 1948.
• 4、 Reinecke et al.. "-". . p. 1365. Retrieved 1973.
• 5、 Hansch. "-". . p. 2908. Retrieved 1947.
• 6、 Yu, Sara Y.,Li, Wei,Iglesia, Enrique. "Desulfurization of thiophene via hydrogen transfer from alkanes on cation-modified H-ZSM5". . p. 257 - 261. Retrieved 1999.
• 7、 Deryagina,Sukhomazova,Levanova. "Competitive reactivities of vinylthiyl radicals thermally generated from haloethylenes and hydrogen sulfide". . p. 662 - 666. Retrieved 1996.
• 8、 Roberts et al.. "-". . p. 3454. Retrieved 1963.
• 9、 Bauer, L. N.,Ermilova, E. V.,Aksenov, V. S.. "New Method for the Preparation of Unsubstituted Benzo- and Naphthothiophenes". . p. 112. Retrieved 1983.
• 10、 Clark,Kirk,Yee. "An improved synthesis of benzo[b]thiophene and its derivatives using modified montmorillonite clay catalysts". . p. 1936 - 1938. Retrieved 1995.